Shelter Island Vacations

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Where to stay in Shelter Island

Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island
Welcome To The Beach. Driftwood beach hut with handwritten welcome sign. Port Crescent State Park. Port Austin, Michigan.

Menantic Creek

If you're looking for some top things to see and do in Menantic Creek and surrounding area, you can visit Sunset Beach and Mashomack Preserve.

Find hotels in Menantic Creek

Find the Best Shelter Island Vacation Packages

Shelter Island Beach Vacation

There's nothing like a Shelter Island vacation to give you a little extra bounce in your step. The sound of rolling surf and the smell of clean ocean air are sure to refresh your mind, body and soul. To be close to the town center on your trip to Shelter Island, find a hotel around Wades Beach (2 kilometers away). If you're planning to stay for a bit, look into our Shelter Island packages. Not only can you save some cash, you'll also have other amazing beaches near you to explore, like Shell Beach and Menhadden Lane Beach.

Shelter Island Hotel Deals

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
The price is ₩913,419 per night from May 28 to May 29
₩913,419
₩1,252,293 total
May 28 - May 29
includes taxes & fees
8.4/10 Very Good! (774 reviews)
Every thing was amazing food and drinks to the fire pits on the terrace area

Reviewed on May 9, 2026

Gurney's Montauk Resort & Seawater Spa
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
The price is ₩220,974 per night from May 26 to May 27
₩220,974
₩281,099 total
May 26 - May 27
includes taxes & fees
Montauk Manor
Montauk Yacht Club

Montauk Yacht Club

4 out of 5
32 Star Island Rd Montauk NY
The price is ₩290,468 per night from May 11 to May 12
₩290,468
₩498,658 total
May 11 - May 12
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
Unhinged wacko

Reviewed on May 6, 2026

Montauk Yacht Club
See all 4,781 properties in Shelter Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Discover the most popular places to visit in Shelter Island

Havens House

You can spend an afternoon browsing the exhibits at Havens House during your trip to Shelter Island. Stroll along the area's beaches or simply enjoy its wineries.

Havens House

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.